A new family of enantioselective dirhodiumn(II) catalysts have been developed by Professor Michael P. Doyle at Trinity University using a rational approach employing molecular modeling and molecular orbital calculations. These catalysts show an extraordinary ability to enantioselectively catalyze a number of different organic reactions, allowing the convenient synthesis of a number of otherwise difficult to obtain enantioenriched materials. These catalysts are excellent candidates for commercialization, showing high yields, enantioselectivities, and turnover numbers, and a degree of ruggedness which permits catalyst recovery and reuse. The specific aims for Phase I are: (1) To transfer the technology for catalyst production and use from the Doyle laboratories to Regis, and to prepare scaled up quantities of the catalysts Rh2(5R-MEPY)4 and Rh2(5S-MEPY)4 for use in application studies; (2) To use these catalysts to prepare selected products of cyclopropanation and intramolecular C-H insertion reactions; and (3) To use chiral chromatography as a tool to upgrade the products of these reactions from high enantioenrichment to enantiopurity. Phase I and Phase II grants will provide an opportunity to demonstrate the utility of the Doyle technology for the commercial production of highly useful enantiopure organic intermediates and pharmaceutical products.